This World versus the World to Come

Once, on the eve of Passover (some say on the eve of Yom Kippur), while R. Hiyya the Elder and R. Simeon ben Halafta were seated studying Torah in the great house of study in Tiberias, they heard the sound of people running about in excitement. When R. Simeon asked R. Hiyya, "What are these people doing?" R. Hiyya answered, "He who has money is purchasing [what he needs for the festival], and he who has no money is running to his employer, who gives it to him." R. Simeon said, "If so, I too will run to my Master and He will give it to me." He went out and prayed in a cave in Tiberias, and beheld a hand holding out a pearl to him. So R. Simeon took it to our Rabbi, who asked him, "Where did you get this? It is priceless. Take these three denars--go and prepare food in honor of the day, and after the festival we shall advertise it, and you will take whatever money it brings in." R. Simeon took the three denars, went to make his purchases, and then came home. His wife said to him, "Simeon, have you turned thief? All your possessions amount to no more than a hundred meah. How were you able to make all these purchases?" He replied, "They were made out of what the Holy One provided." At that, she said, "If you won't tell me where you got the money, I will taste nothing at all." He told her, "This is what I prayed to Heaven for and what was given me from Heaven." She said, "Do you wish that your canopy in heaven should have one pearl less than that of your colleagues?" When he asked, "What shall I do?" she replied, "Go and return your purchases to their owners, the denars to their owner, and the pearl to its Owner." When our Rabbi heard that R. Simeon was grieved, he sent for his wife and said to her, "You have caused much anguish to this righteous man!" She replied sharply, "What do you want--that his canopy should have one pearl less than yours in the world-to-come?" He said to her, "And even if it should, will not one among us make it up to you?" She answered him, "Rabbi, how do we know that we will be privileged to see your face in the world-to-come? Will not each and every righteous man have his own chamber?" Rabbi admitted that she was right. As soon as R. Simeon heard what Rabbi had said, he went and returned the pearl.

Here is another bothersome story. There are two issues:
First, The idea that any good things that we use on earth, will not be available to us in heaven. Therefore being poor is good. In a very poor society such a theory can provide hope and justification for those who are very poor. We in a currently rich society take having things for granted and tend not to think that being very poor is good. However Rabbi is included in the story and he was exceedingly rich yet he would also have his own chamber in the world to come.
Second, the gift of the pearl would not mean that R. Simeon ben Halafta would be poor or miserable in Olam Ha-ba but that his canopy would have one less pearl. It sounds more like a status thing than a real loss. Since he seemed to be one of the poorest of the scholars shouldn't he have had much more to start with?